Q is for the quirt I use to whip your eager ass
by SuperWoman0124
Summary: Someone in Sam's school says they'll give him 500 for a pair of Dean's boxers. Dean says it's really Sam who wants them. Gives him a choice. Whip or fuck. Lessons are learned. A love story.


Title: Q is for the quirt I use to whip your eager ass

Summary: Someone in Sam's school says they'll give him $500 for a pair of Dean's boxers. Dean says it's really Sam who wants them. Gives him a choice. Whip or fuck. Lessons are learned. A love story.

Characters: Sam W./Dean W. OC

Tags: Unrelated Winchesters, Unrelated Dean Winchester/Sam Winchester, High School AU, Top Dean, Bottom Sam, Underage Sex, Sam is a freshman, Dean is a senior, but it's never really discussed, Jock Dean, Nerd Sam, First Time, Anal Fingering, Rimming, Anal Sex, Spanking, Happy Ending

Notes: Image Credit goes to: Season 12 Screencap

In October of '14, I began a collection titled "The Abc's of Kinky Sex" (based upon The Lords of Acid song of the same name) where I took each of the 26 letters (Different ships & fandoms) and made a fic about each line. It took me almost 7 months to finish, but I never posted Z. Doing a little facelift and posting to this website as well. Enjoy!

Original Notes: Warning; Some mentions of child abuse.

This flowered into something I totally didn't mean it to. There was supposed to be little to no plot and a quick rough fuck, but I kind of fell in love with the characters I was creating. Plot evolved. I've even considered writing another chapter and making this into a real story, but alas, all good things must come to an end. It's more of a love story than the kinky love fest that I meant it to be. I apologize.

It's been almost a month since I've posted here, but to be fair, I did write two one shots in the mean time. [Complacent Kisses + A Happy Birthday, Dean fic that I'm holding off posting until his actual birthday. *u* ] Plus this fic is like, 6K+ words long.

"Dude, Dean is so hot." Dave leaned over in Geometry class, tapping his pencil against the edge of the desk. "How have you not tried to hit that?"

Sam rolled his eyes. Here we go again. "One, He's my much older neighbor. He used to babysit me when I was like 6. Two, He's a football jock that would never go for a geek like me. Three, and Dave, listen closely, and for the last time, I'm not gay!"

Dave sat up straight and whispered, "Sure could have fooled me."

Sam flipped his hair back and whispered angrily, "I swear to god, you mention that one time we drank too much and made out behind the shed at my aunt's, I'm going to murder you."

Dave snickered, but Sam knew the argument wasn't over. Every time Dave mentioned that Sam was gay, he didn't let it go for days. Sure, Dean was attractive. His leather jacket and crew cut hair, the smile that made him want to melt and turn into goop, and those eyes... It wasn't just about looks though either. Dean was a really nice guy for a jock. He was courteous, kind and gentle. He also had this strange sense of humor that Sam abundantly hated but secretly loved. Sam originally thought it was jealousy but eventually, he realized...

The bell rang abruptly, knocking Sam out of his imaginative stupor. He shook his head and gathered his things. Dave led the way out the door and Sam followed behind.

"I'm just sayin', I've seen the way he looks at you. You should give it a shot!" Dave hopped to show his excitement. The walk home was always great with Dave, but it was times like this he wished he lived closer. "And hell, if you won't, I will. I bet you he smells like leather and aftershave."

Sam eyed Dave like he's never heard anything crazier in his life.

Dave looked over, smirking.

"I bet you his boxers smell like heaven."

"Dude, gross!" Sam elbows Dave in the chest, knocking him farther to his right.

Dave cupped his hands together and held them to his nose, inhaling deeply, pretending Dean's boxers were in his hand.

"Dude, I'd pay any amount to just get a whiff of what that guy's packin'."

"Really?"

"Hell yeah!"

"Like, how much?"

Sam had been known to do dumb things for money. Some people thought he was just gullible. In all reality, it had been for college. He wanted to be a lawyer, and his parents couldn't (wouldn't) afford it. So anytime situations such as this arose, Sam knew he'd say yes. He'd always say yes.

"I don't know..." Dave stared into the distance, knowing that Sam would do it for any amount, but Sam also didn't know that Dave knew he was saving for college. "$500?"

"You're shitting me!" Sam waved his hand in the air and walked a little faster, gripping his backpack.

Dave sped up, "Seriously, dude! You know I'm good for it. I still have my birthday money!"

"You wanna spend your birthday money on a pair of sweaty ol' boxers, you freak?"

"Nah, man. I wanna spend my birthday money on Dean Winchester's sweaty old boxers."

Sam stopped and turned towards Dave, sighing. "You're sure?"

"Yeah, Sammy." Dave shot his brightest smirk.

"Don't call me Sammy. It's 'Sam.'" No one calls him Sammy. He wouldn't even let his best friend use the baby-ish nickname.

Sam, reluctantly, stuck out his hand and Dave took it.

"I so know I'm going to regret this." Sam rolled his eyes and walked away.

The good thing about covertly stealing his neighbor's underwear was he was pretty familiar with Dean's routine. He normally got home around 4, showered, then went out to go shoot pool with his friends. Sam would wait until shortly after 5 so his parents wouldn't suspect his absence at dinner at 6:30. He really didn't feel like taking another beating for being late to dinner.

Sam pulled his homework out of his book bag and dropped it onto his desk, opening his geometry book and looking at the clock. 4:15. He had about an hour before he had to leave. He looked down into his book and tried hard to read the question. He found that he had to read it again, and again. He couldn't focus. He looked back up at the time. 4:20. Only 5 minutes had passed. Sam stood up and bounced, shaking his fingers and arms to get his blood moving.

"Focus, focus, focus." He whispered to himself. "You're just nervous about sneaking into your neighbor's house." The pep talk was working and he was starting to feel better. Sam stopped jumping and sat back down at his desk, persistently focusing on his homework.

His 15th question in, he looked back up at the clock. 5:30! Shit!

Sam closed his book and pulled the black hoodie off of his door, pulling it over his head and pushing his sneakers on as fast as humanly possible. He pulled open his wooden window frame roughly, causing a loud squeak to emanate through the room. He kicked his leg out until he felt the grass underfoot and pulled the other leg out. He took a second to collect himself and catch his breath before tiptoeing the 10-feet or so over to Dean's bedroom window. The lights were off and it appeared as if he'd already left. His dad's Impala wasn't in the drive-way, so he must be safe. Sam stretched his arms up and lifted the glass in the window, then the screen and jumped up, the window ledge catching his torso. He flailed for a moment, kicking his legs to get leverage and found himself swinging his arms. He finally got a hold of the wall, and pulled himself in.

He'd been in Dean's room a couple of times since they were kids and everytime he was in there, it seemed different. He found his footing and was stood up when he noticed the poster size "Budweiser Babe" half naked and posing, clung to his wall. Sam suddenly felt what he could only describe as disappointment. Sam shook his head, clearing his thoughts for the task at hand.

He looked to his right where he found the 4-drawer dresser and walked over to it. He yanked on the first shelf and found T-shirts, tightly wound into tubes and tucked together. He opened the second shelf and found what he was looking for. Dean's boxers to the left and his socks on the right. Sam pulled one of the pairs out and went to turn around to leave. He stopped. Dave didn't want clean underwear. He wanted dirty ones. Damn it.

Sam spotted Dean's dirty hamper in the corner of the room and silently crept over. He flipped the top and pulled some clothes out. He found a pair of navy blue boxers. They were normal. Stitched crotch and gray waistband. Hell, Sam thought he had the same pair himself. But these, these were special. They were Dean's. He found himself lowering until the back of his knees hit the bed and he raised the boxers up in his fist. Oh god, he wasn't about to do this. He was so curious. And no one else is here.. Who would find out? So gross..

Sam shut out the mixed voices in his head and raised the boxers up high enough so he could sniff lightly at them. It actually smelled pretty good. It smelled like Dean and his cologne. Sam brought it closer and he swore he could smell Dean's sweat and... and... something else. He just couldn't.. and before he realized, he was shoving his face into the boxers trying to identify the smell.

That's when he heard the bathroom door pop open.

When Sam lowered the boxers, all he saw was Dean's partially naked figure, standing in a towel and slicked wet from the shower.

"What the fuck, pervert!?" Dean raised his right fist, ready to start swinging. Sam put his hands up, surrendering and dropped the boxers.

"It's not what it looks like!" Sam shouted. "I can explain!"

Dean stopped, half-cocked and stood straight up, crossing his arms across his chest.

"The only reason I'm not ghosting you is because we used to be so close. You've got one chance, Sammy. I'm listening."

Sam looked down, and when Dean called him "Sammy" he didn't want to correct him. He liked the way Dean said it. It sent shivers down his spine. When he looked up, he observed the flimsy white towel wrapped tightly around Dean's waist and the way the moisture glistened in the overhead light. He tried to swallow, but something in his throat seized.

"Earth to Sammy." Dean waved his hand in front of Sam's face. "You've got about a minute before I turn you over my knee and spank you so hard, you'll cry for a week."

"It- uh." Sam chewed on his bottom lip. "It was a dare;" Sam fiddled with the material between his fingers. "My-my friend said he'd give me $500 for them. He's-" Sam looked down and scanned Dean's body on the way back up. "He's kind of in love with you."

"He's in love with me, huh?" Dean took a step forward. "Sure you're not making this up so you could come in here and sniff my panties?"

"Fuck no!" Sam exclaimed, loudly. "I mean, n-no." Sam suddenly became fascinated with a speck of dirt from his shoes on the floor and didn't dare, not for anything, look up.

"Alright. I believe you." Dean relaxed, letting his arms fall to both sides. "But I still have to make sure this never happens again, capeesh?"

Sam nodded quickly, still not looking up. "Are you gonna tell my parents?"

Dean strolled over to another set of drawers on the other side of the room and opened the bottom one. Dean had a black safe in there. Putting in the combination '11-2-83', the lock clicked open and he pulled it up. He pulled out something black and leather, Sam's eyes straining to see out of his peripheral vision.

"No," Dean stood straight up, laying the object on the edge of the bed. Sam still couldn't see it. "and I know you won't tell anyone what happened tonight. Why would you? So, I'll give you a choice. I can either... use this..." Dean picked the object back up and moved it closer to where Sam could see. The second Sam noticed that it was a long, leather whip, his eyes blew wide. He didn't want to be whipped. He'd been on the wrong side of his Dad's belt one too many times, and he didn't want that one bit. Nuh uh. Sam finally looked up and suddenly Dean looked like the most amazing thing on the planet. His eyes were wide and sparkling and Sam wanted nothing more to get out of here so he could go home and jack off in his shower.

"Or, uh-" Dean turned on his best smile, running his hand down his stomach. "I could teach you a lesson."

"What's the lesson?"

"I won't tell you until you agree."

"Well, I don't want to be whipped, so..." Sam shook his head profusely. He didn't think a firm talking to measured up to a whip so he pondered. It didn't take much thought. " I'll take the lesson."

Dean ran his tongue over his bottom lip unconsciously and nodded tightly.

"I was hoping you'd say that. " Dean rocked back and forth on his heels. "Stand up, Sammy."

Sam huffed, but did as he was told.

Dean moved closer to him, his towel parting when he put his knee forward and Sam saw a glimpse of his upper thigh before the towel moved back in place.

Dean stood in front of Sam and got close, but ducked to his right and sat on the edge of the bed.

Dean tapped on his lap twice.

Sam now remembered the beginning of the conversation where Dean talked about spanking him. Shit, Sam. Keep it together. Now is not the time to get a hard on.

Sam went to kneel beside Dean's legs and Dean tisked.

" Bare."

"You want me to take my pants off?" Sam was shaking where he stood.

"If you wouldn't mind. Hoodie, too." Dean looked up and sent Sam a charming smile and a wink, making Sam want to melt on the very spot. Instead, he walked across the room and took down his fly and button, wiggling his pants to his ankles. He covered his half-interested cock with his hands, and kicked his pants off to the side. Sam removed one hand from his crotch to pull it out of his sleeve, then switching hands to do the same to the other arm. He realized that he wouldn't be able to pull the hoodie over his head with one hand, so as quick as possible, he yanked it off and threw it with his pants, returning his hands on his bulge.

Dean eyed the young neighbor's half naked body and whistled.

"My, my Sammy. How you've grown. Last chance to change your mind."

Sam mindlessly moved closer, bathing in the glow of the praise. Sam lowered to his knees beside Dean and stretched himself over his lap. It felt awkward, and he suddenly felt like a child, dwarfed by the large size of Dean's thighs. Sam readjusted himself so his swollen cock wasn't rubbing across his leg.

"Tell me, before we move forward. And I'll know if you're lying. Do you think I'm..." Dean felt embarrassed asking the question. He knew he was attractive. A majority of the school fawned over him, students and teachers alike, but he didn't know if he appealed to Sam. "Do you think I'm attractive?"

Sam tried to turn his head, but it was difficult in this position. "What?"

Dean swatted hard against Sam's nude globes, turning the flesh pink on contact. Then, a slap between each word.

"Do..." Smack. "you..." Smack. "think..." Swat. "I'm..." Slap. "sexy?"

Sam huffed, crying out with each landing blow.

"What the fuck, man? You don't gotta do it so hard." Sam turned to face Dean and Dean wiggled his left knee under Sam, unintentionally stroking Sam's now fully hard girth.

"You don't seem to mind." Dean ran his hand down Sam's flank. "Just answer the question, Sammy."

Sam looked down, directly staring at the bed sheet below him. Sam stifled the urge to cry out, stuttering his response. "I'm n-not gay."

Dean reared up and smacked him twice. "I told you not to lie." Dean growled.

"I'm not lying!" Sam started squirming in his lap, fat tears rolling down his cheek. "I'm not gay! I swear! It's-It's just..." Sam buried his face in the sheet below him and whispered, hoping Dean couldn't hear him. "It's you. The only male I've ever found attractive is you."

Dean could feel the blush rushing to his face. Admitting that took a lot of balls. Dean smoothed his hand down the heated flesh of Sam's bum, and appreciated the little gasp that left Sam's lips.

"So, you do like me?" Dean smirked down, hoping he wasn't assuming anything.

Sam still had his face buried in the bed when he replied with a sigh and a one-word answer. "Yeah."

Dean laid his hand on Sam's chest, pulling him up. Sam stood, both sets of cheeks red and swollen and his cock was barely contained by his boxer briefs. His face, shined with innocence as Dean stood and moved closer. Dean grabbed his equally hard cock through his towel, and rubbed himself just long enough to make the ache go away. Dean brought his hand up to the back of Sam's head and clenched his fingers in his hair.

"I'm supposed to teach you a lesson." Dean huffed through clenched teeth.

"Yes, sir." Sam nodded tightly, running his thumbs in circles over his crotch.

"You a virgin, Sam?" Dean ran his hand lightly down Sam's cheek, making Sam visually shutter under the contact. Sam blushed and tried to turn his face away, but the tight grip Dean had on his hair stopped him.

"Yes, sir." Sam sniffed.

"Why haven't you lost it?" Dean stepped closer, clutching on his hair and pulling Sam's head to his left, allowing Dean access to his neck. Dean kissed Sam's shoulder lightly and when Sam didn't push him away, he kissed a line all the way up to his neck. Sam gasped and shivered.

"'M savin' it for someone special."

"And who's special in your book?" Dean parted his lips and began open mouth kissing Sam's shoulder.

"Y-you." Sam keened, unable to control what he said, wanting to come so badly just from having Dean so near him.

"Me, huh? Well, Sammy, I'd be honored. Have you ever even kissed someone?"

"Uh-huh." Sam closed his eyes and nodded, breath shuttering as Dean worked his way up Sam's neck again. "Couple times."

"Any boys?" Dean kitten licked the indented space on Sam's collar bone. Sam was visibly shaking, so turned on it hurt, and Dean had never seen anything so innocent and beautiful.

"Once." Sam gulped. "My best friend. Drank too much." Sam let out an exasperated breath. "That's how I know I'm not gay."

"That bad, huh?" Dean pulled himself back and looked into Sam's glowing hazel eyes, licking his lower lip.

"It was..." Sam smirked. "Absolutely terrible."

The laughter that came seemed to curb the tension between them a bit, and Dean straightened his back before continuing.

"Care to try it on me? I've been told I'm an amazing kisser."

Sam shifted on the balls of his feet. He wanted to pinch himself to see if this was real. If this was actually happening. He'd had this fantasy way too many times before. He covered his crotch with the palms of his hand, willing his raging and very obvious hard dick to go down.

"Is this part of the lesson?" Sam shivered in Dean's arms, goose bumps rising in the spots he was bare.

"I think we're kind of passed that. Don't you? I mean, I did just spank you." Dean chuckled and ran his fingertips down Sam's arm.

"Good point."

Dean licked his lips again, and moved an inch closer. "So? What'll it be?"

"I suppose I could try again." Sam smiled, playing coy wasn't exactly his strong point, but he would have done anything to make this happen.

Dean quickly leaned down and captured Sam's lips, wrapping his arms around Sam's torso like he was going to turn away. Sam moaned into Dean's open mouth, wrapping his arms around Dean's neck. Dean pulled away and bit his bottom lip, suddenly self-conscience.

"Whoa."

"Whoa is right." Dean smirked, the lady-killer grin finally coming to the surface. "So, about this lesson.."

"We're still on that, are we?" Sam smiled, chuckling lightheartedly.

"Well, what have you learned?"

"That doing a B&E can get you a kiss from the crush you've had since you were a kid?" Sam pushed his palm into Dean's chest, knocking him back lightly.

"No, Sammy. This is serious now. You shouldn't have snuck in like that." Dean laced his fingers into Sam's, separating them until his arms rested at his sides.

"What was I supposed to do? Ask?" Sam shifted, biting his lower lip.

"Yeah! Why not? Could have split the cash with me." Dean winked. "Seriously, now. It may seem weird to you, but I need to follow through. I'm gonna fuck you." Dean reluctantly dropped Sam's hands and ran one down Sam's cheek. "That's a forewarning. If-" Dean took the tied corner of the towel between his fingertips and pulled. The flimsy towel cascaded to the floor, and Dean placed his hands on his hips. "If that's okay."

Sam bit his lip and nodded shyly. He'd never been more nervous in his life.

"My methods may be unorthodox, but trust me. It'll be great. If at any time you want to stop, say so. I won't be angry or upset. I'll do all the work." Dean palmed Sam's cheek in his warm hand. "You okay, Sam?"

"'M just nervous." Sam smiled lightly.

"Yeah, that'll happen." Dean took the necessary step forward and kissed Sam again, Sam letting his lips part to allow Dean's tongue the access it needed. Sam visibly shook, but the second the older jock's fingertips hooked under the hem of Sam's shirt, he stopped, and removed his hands from his crotch to place them on Dean's shoulders.

Sam shuttered, not used to the sexual tension hanging in the air. He ran his hands down Dean's side and let himself be controlled through the kiss. Dean pushed him back a step, until he was sitting on the bed. Dean was still on him, mouth possessing, as he ran his hands up Sam's muscled chest.

Dean leaned over him, running one hand through the younger man's hair and ran a hand over his own engorged cock, and moaned. The vibration shattered Sam, unintentionally returning the moan. Dean stood up and took Sam's hair in both hands, pulling his head toward his crotch. Sam fell to the floor on his knees, and Dean removed one hand from his head to offer his cock to Sam.

"You good, Sammy?"

Sam looked up into those bright green eyes and breathlessly nodded.

Sam leaned forward and licked the very tip. The precum dipping off was salty but he went back and licked all the way from the shaft to the head. Dean's head fell back and he let out a subtle grunt. Sam parted his lips and wet them, taking the head into his mouth. Dean's fist clenched in his hair. Sam pushed himself farther down until he couldn't take anymore, and Dean tipped him back so his head was hitting the mattress.

"I may get too rough. If it's too much, remember, just tap on me. I won't be mad."

Sam tried to reply around the cock down his throat, but instead just nodded, looking up into those devilish green eyes staring down at him.

Dean began, slowly, shoving himself down into the tight enclosed heat that was his little Sammy's mouth as he struggled for breath. He wasn't choking, which he thought he would be. Just the thought that this was actually happening made him want to do it better, prolong the abuse to his throat longer.

Dean began to dip down and Sam could feel Dean's balls slapping against his chin, saliva dripping down his chest. Sam could hear the moans being ripped from Dean's belly as he fucked in, pumping in and out of his mouth.

Dean suddenly stopped, pulling his cock out and moved up, straddling his face until Dean's tight puckered hole was in its place. Sam lapped at it questioningly, curious about what Dean was doing, but when Dean began to squirm, Sam figured that it felt good, so he kept going. Sam poked his tongue in and Dean rode it, and began spouting words uncontrollably.

"Fuck, fuck, fuck, Sammy. Feels so good, so fucking good. Can't wait to do this to you, can't wait to taste you and stick my hard cock in that tight ass of yours." Sam began to feel hot, his cheeks burning at the dirty talk, so he reached down to palm at his throbbing prick through his underwear. Sam formed his tongue as straight as he could and poked up, making Dean moan louder than ever before. Dean stopped again, rolling off of Sam and placing his hands under Sam's arms and pulling him up on the bed.

Dean grabbed him roughly, turning him over on his stomach, slapping one of Sam's firm globes harshly. Sam moaned, forcing his face into the mattress to hide the blush spreading across his face. Dean admired Sam's ass, taking the elastic of Sam's boxers down his hips and off his legs. He pulled them passed his ankles, kissing his left hip as he passed. Dean spread both cheeks in both of his palms, revealing the warm pink hole between them.

Sam bucked back wildly, curling his fingers into the soft blanket. Dean spanked him again, raising a surprised yelp from the younger neighbor. Dean massaged him, opening and closing his cheeks, a mesmerizing pace that Sam soon became comfortable with. Dean pulled him open particularly wide and Sam felt something wet lick a stripe up his hole. Sam thrusted his cock into the mattress, the stimulation too much to bear so he focused on catching his breath.

"The fuck was that?" Sam heaved, looking back as far as he could. He saw Dean's smirk, going back to lick up Sam's crack again, making him moan.

"That," Dean probed his tongue in, swirling the tip into the tight wet heat. "Was my tongue-" another swirl, and a lap. "In your ass." Sam gasped, clenching the mattress to stay grounded.

"Fuck, Dean. So... so hot." Sam squirmed under the undivided attention, suddenly self- conscience about the way he tastes. Is he gross? Did he wash well enough? Obviously, Dean thinks so because he's now tongue fucking him in earnest, spreading his wide palms over Sam's lower back.

"Taste so good, Sammy." Dean lowered his hand, gently spanking the left firm ass cheek. Sam's mouth is wide open, panting, grinding his hips down for friction. Dean moved his index finger to circle the rim, making Sam's hair stand on end. Dean pushed in without warning, all the way to the first knuckle.

"Ah! You could warn a guy!"

"I told you I was going to fuck you." Dean huffed his response, chuckling lightly while he licks the taste of Sam off his lips. "You didn't think I was just gonna shove in guns blazin', did ya?"

"N-No, I guess not."

Dean pushed farther in, the burn spreading everywhere, making Sam hiss and try to pull away. Somehow, when Dean saw that Sam was in pain, the tender side of him came back.

"Yeah, I know, Sammy." Dean rubbed his free hand over his lower back. "Breathe through it. Relax. Stay with me. It'll get better." Dean pushed farther in, more gently and crooked his finger just so.

Sam bucked forward, the sudden pleasure is so sharp and urgent, it's almost pain but it feels so good, so right that it builds and builds until Sam lets out a subtle gasp.

"Fuck!" Sam shoves back onto Dean's finger, craving more, craving something, anything, as long as Dean keeps touching that spot. "Do-do that again."

Dean pushes back in and smirks, applying light intense pressure to Sam's prostate. "This?"

Sam gasps and thrashes and goes out of his mind, throwing his head back and hyperventilating, trying to make coherent words that won't form on his lips. Sam squirms under Dean and Dean keeps pushing in, wiggling the tip. He pulls out and Sam moans at the loss of the fullness, but is not surprised when he feels two fingertips resting at his entrance.

"Ready?" Dean whispers, leaning down to softly bite one cheek, making Sam smirk and gasp.

"Yes." Sam's hands were shaking with the intensity. He was gripping the sheets, preparing himself and trying to relax at the same time.

Dean lightly nudged in, the stretch and burn dispersing up Sam's spine and making him quiver. The jock kept pushing, strong arms glistening with the sweat of holding back, gleaming as he twisted in, scissoring his fingers apart. Sam hadn't realized...

"Dean, have you done this before?"

Dean leaned forward, spreading his fingers and lapping at the space in between, stalling to come up with an answer.

"Not really. But, I know what I'm doing."

Sam shook, Dean lightly tapped on the spongy round space inside, alternating pressure. Sam keened when Dean pushed lightly, nearly screamed when Dean shoved heavily.

"Then how-?" Dean knew the question was coming before Sam did, trying to put together the courage to say it.

"I've had it done to me." Dean said sullenly, readjusting his focus to Sam's delightful ass and plunging his fingers faster.

"Oh." Sam didn't know what to think. He didn't have long to think about it either because Dean was pressing in, fucking him on his fingers and hitting that spot every thrust in.

"Obviously I'm not doing my job very well if you can still form coherent sentences." Dean pulled his fingers out too soon, making Sam want to curl into a ball and cry. The emptiness he never thought he would experience, but something he know knew he could never live without again. Dean pulled his knees up, his pulsing cock sliding along Sam's open hole, waiting, contracting, inviting.

"D-do it, Dean." Sam peered over his shoulder at the older man, who looked like he was second guessing himself. He was about to take this boy's virginity. Had he done that before? Had it ever mattered to him so much? Had sex ever mattered to him this much? He suddenly felt a bead of sweat roll down his back in a cold panic, eyes popping wide.

Sam bucked back, taking Dean's fleshy head into himself, letting out a short hiss and then a groan, knocking Dean out of his wondrous stupor. Dean shook the fog off, landing a loud smack to Sam's pleasant rear, making Sam gasp. Dean didn't dare move, fear and panic taking over his overall cocky nature. Sam was whining, clenching his fingers into the sheet as he rocked back. A hint that Sam wanted more.

Sam finally took initiative, sitting back until all of Dean was inside of him, ripping a moan from Dean's unsure throat. Dean refocused his attention, leaning over to pepper kisses over Sam's unblemished back, hands roaming on his naturally bronzed shoulder blades and timidly rolling his hips in circles, teasing at Sam to hear his reaction. Sam made the most beautiful sound Dean had heard in his life. On the intake of breath, Sam moaned gloriously, making Dean tilt his head back.

"D-Dean... Can't.." Sam shuttered visibly.

Dean ran his hand down Sam's side, shushing him with a soft undertone. He swiveled his hips, pulling himself halfway out before letting Sam readjust again, confirming that he'd done the right thing when Sam let out a subtle moan. Dean pushed himself back in, taking aim for that special little place inside again, hitting it straight on. When Sam gasped, his arms weakened and he fell forward, laying his head against a pillow on the bed. Dean pumped in, laying his warming hand against the smooth curve of Sam's hips, clenching way too tight for how silky Sam's skin is. Sam shutters again, too much, too slow, need, need, need.

Apparently, Dean's a freakin' mind reader, or Sam had said it out loud, he wasn't sure, but the constant push/pull of Dean's cock inside had sped up, plunging deeper with each practiced thrust. Sam huffed, reaching down to reach for his own half hard cock, deflated from momentary pain, stroking the tip to get it back to full hardness, and smearing the dripping precome down the shaft. Sam closed his eyes, bouncing with every sharp thrust and wanting to scream his pleasure. He bit back the loud moans that wanted to escape, not knowing if Mr. Winchester was home or not.

Dean threw his head back. He knew that all to shortly, the end would be here. He saw and slowly approached the end of the cliff, all while stuffed into the tight, wet heat of his neighbor. Sam pushed himself up, slotting his shoulders on Dean's chest, not stopping, not for anything, so close, and Sam reached behind Dean to grasp at his short crew cut, gripping at the short hairs to pull Dean in for an awkward sloppy but sensual kiss. Dean's grip on Sammy's hips grew tighter and tighter as the kiss deepened, allowing his tongue to be massaged with the younger's. Sam let out little gasps while he stroked himself, hips stuttering, hands shaking, until finally, Sam came, white hot streaks cascading over his knuckles while he hyperventilated on Dean's dick, causing the tight spasms that made Dean see stars. So tight, so hot, too much. **Too much.** Suddenly, Dean felt like he was smacked with a bag of bricks while his orgasm spread a strange warmth over his body, emptying himself in the velvet walls before him, while Sam stole his breath with little kisses to his slack lips. Dean's vision went black and he suddenly felt tired.

He finally came to, Sam still licking into his mouth and kissed back, leaning his forehead against Sam's shoulder. Sam fell forward, balance all off as Dean pushed his weight and he rolled off of Sam's small frame, afraid to crush him. He tried to catch his breath, chest heaving from the exertion, a little chuckle escaping his overextended lungs. He stared at the ceiling, listening to Sam's heart beat beside him, smiling like the cat that ate the canary. Sam looked at him, wide eyed and smirking, letting out a deep sigh. He rolled over, leaning his brown locks on an open palm, using his elbow as an anchor.

"W-was that-" Sam huffed, the blush rushing to his ridiculous cheekbones and Dean wanted to kiss that silly stupid smirk so bad- Dean knew what he was going to ask.

"It was fantastic, baby boy." Dean laid one hand over Sam's, leaning forward to place a light kiss on his cheek.

"So, was that like," Sam gulped. "A one-time thing?" Sam got the words out as fast as possible, afraid he wouldn't get them out otherwise.

"Do you want it to be a one-time thing?" Dean was taken aback, he laid back down to play it cool, crossing his arms over his chest.

"Well- I-I don't- I mean," Sam suddenly became fascinated with picking at a ripple in the sheet. "Not really."

"Then it won't be." Dean shrugged. No big deal, right? It's not like Dean's been fantasizing about this very moment since Sam began puberty. Hearing the little cracks of his voice out the window while Dean did his homework. Seeing Sam begin to shoot up tall like a bean stalk. [Sam had grown 2 inches in the last 6 months!] Become a man. That's why they'd stopped hanging out. It scared Dean.

"S-so, you're my boyfriend?" Sam inched closer, watching Dean's reaction.

"We'll see." Dean pushed on Sam's shoulder in a friendly nudge, the smile creeping up his face. Sam kicked back with a sigh. This was probably the happiest moment of his life.

"SHIT." Sam shot up, looking at the alarm clock on the edge of Dean's shelf. 6:45 shone brightly through the room. Sam was late to dinner. "Shit, shit, shit!" Sam muttered under his breath, instantly up, out of bed and looking for the strewn clothes amongst the bedroom.

"What's the matter?" Dean's sleepy demeanor gone, replaced with panic and worry.

"I'm late for dinner! My dad is gonna kill me!" Sam found his pants, but no boxers. Where the hell were his boxers? Fuck it. He threw the one pant leg on, jumping in the other and fastened himself as quick as he could. He pulled the hoodie over his head, searching his for anything he might have forgotten. Sam realized it was all there, sans boxers, and sighed. He quickly bent over Dean's spry body, kissing Dean's lips chastely before rushing to the window. He spared one final glance back at the jock who stole his heart, eyes gleaming.

"See you tomorrow?"

Dean nodded tightly. "Yeah. After school. And Sammy?" Dean smirked.

Sam lifted one leg out the window, looking back. The boxers Sam had been sniffing were suddenly thrown at his face, landing on his stretched legs.

"Don't forget those." Dean winked.

Sam couldn't wipe the smirk off his face if he tried.

Little did Sam know, that Dean found his boxers under the bed and curiously held them to his face, finally knowing what all the fuss was about. Dean crumpled them in his fist, falling asleep with thoughts of Sammy climbing back into his window and snuggling up.

-Next Day-

"Dude, why won't you tell me? I mean, you got Dean's boxers and all, but what's with the cheery attitude? Why are you so fucking happy? Not that I'm not happy for you, but damn, dude-" Dave bounced beside him between classes, study hall next.

"Dave, calm down. Everything's fine!" Sam sniffed, rolling his eyes. "And stop calling me dude!"

Sam hadn't seen Dean all day and he was getting pretty anxious. He'd expected Dean to come around every corner, adjusting the shoulder straps of his backpack and gleaming those pearly white teeth at him. But, no Dean. Still didn't stop him from giggling like an idiot when the thought arose. Study hall was terrible, but he'd finished all his homework in the first half, not wanting to have to do it when he got home. Devoting all his time to that stupid jock next door. Sam began to space out, and soon the bell rang, signaling the students that school was done for the day. Dave followed suit, tailgating Sam in the hallway full of pushing students and yelling teachers, all into the bright afternoon sunlight.

When Sam looked up, he saw Dean, smiling brightly and staring directly at him, hips pressed into the black paint of his father's Chevy Impala. Sam didn't think his smile could have been wider until Dean opened his arms as he approached, accepting the small teenager in for a long hug. When Sam looked up, unsure about this obvious public display, Dean captured Sam's lips with his own, wrapping his arms tightly around his small frame.

"Where were you?" Sam whispered into Dean's chest.

"Senior skip day." Dean shrugged, smelling like leather, aftershave, sweat and just Dean. "Thought you knew! Com'on. I'll take you home."

When Sam turned around to wave goodbye at Dave, Dave stood, 6 feet away, mouth wide open and jaw on the pavement.

Sam pulled on Dean's hips, turning to face Dave.

"Dave? I think you've met my **boyfriend**, Dean."

Sam was happier than he ever had been. It suddenly made the sore red belt welts his father left the night before all the more bearable. He'd take more, if it meant that he could spend more time with his stupid jock neighbor, his un-resistible, kinky, football star boyfriend.


End file.
